(2E)-1-(2,4-Dimethyl­quinolin-3-yl)-3-phenyl­prop-2-en-1-one

Prasath, R.; Bhavana, P.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813004765

Volume 69
Part 3
Pages o428-o429
March 2013

Received 18 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R = 0.066
wR = 0.190
Data-to-parameter ratio = 17.9
Details

(2E)-1-(2,4-Dimethylquinolin-3-yl)-3-phenylprop-2-en-1-one

R. Prasath,^a P. Bhavana,^a ⁺ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, BITS, Pilani-K. K. Birla Goa Campus, Goa 403 726, India,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

Two independent molecules comprise the asymmetric unit of the title compound, C₂₀H₁₇NO, which differ in the orientation of the terminal phenyl ring with respect to the quinoline ring [the dihedral angles are 75.72 (11) and 84.53 (12)° for the two molecules]. The conformation about each of the ethylene bonds [1.329 (3) and 1.318 (3) Å] is E. The crystal structure features a combination of C-HN, C-H [pi] and [pi] - [pi] contacts [inter-centroid between the phenyl ring and the quinoline benzene ring is 3.6024 (19) Å], generating a three-dimensional network.

Related literature

For background details and the biological application of quinoline and quinoline chalcones, see: Joshi et al. (2011); Prasath & Bhavana (2012); Kalanithi et al. (2012); Prasath et al. (2013). For the structures of the isomorphous chloro- and methyl-benzene derivatives, see: see: Prasath et al. (2011, 2012).

Experimental

Crystal data

C₂₀H₁₇NO
M_r = 287.35
Triclinic, $[P \overline 1]$
a = 11.1295 (9) Å
b = 11.5764 (8) Å
c = 13.3989 (11) Å
= 96.176 (6)°
= 112.900 (8)°
= 96.533 (6)°
V = 1558.0 (2) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 295 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.764, T_max = 1.000
14138 measured reflections
7191 independent reflections
3395 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.190
S = 1.05
7191 reflections
401 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C15-C20 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C14-H14N2	0.93	2.59	3.463 (3)	156
C7-H7CCg1ⁱ	0.96	2.86	3.662 (3)	142
C39-H39Cg2ⁱⁱ	0.93	2.88	3.679 (3)	145
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+2, -z+2.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5294 ).

Acknowledgements

PB and RP gratefully acknowledge the Council of Scientific and Industrial Research (CSIR), India, for research grant 02 (0076)/12/EMR-II and Senior Research Fellowship (09/919/(0014)/2012 EMR-I), respectively. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.
Joshi, R. S., Mandhane, P. G., Khan, W. & Gill, C. H. (2011). J. Heterocycl. Chem. 48, 872-876.
Kalanithi, M., Rajarajan, M., Tharmaraj, P. & Sheela, C. D. (2012). Spectrochim. Acta A, 87, 155-162.
Prasath, R. & Bhavana, P. (2012). Heteroat. Chem. 23, 525-530.
Prasath, R., Bhavana, P. & Butcher, R. J. (2012). Acta Cryst. E68, o1501.
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o796-o797.
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013). J. Organomet. Chem. 726, 62-70.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds